The Headless horseman of Sleepy Hollow
by johnnymcallister2000
Summary: Sam and Dean head to a town in England to battle with the headless horseman And save a decendent from Icobod who is important to the angels. Some horseman myths maybe changed and re told. Based after Heaven and Hell in season four
1. Chapter 1

THE ROAD SO FAR:

Dean: I think we were meant to finish what dad started. Hunting, the family business.

Sam: What am I suppose to be Dean? Evil? What because I have demon blood in me?

Dean: So this is Ruby?

Ruby: The demon who is after you. Her name is Lilith. She doesn't like you very much.

Bobby: How long did they give you?

Dean: One year.

Sam: Did you know about Dean's Deal? That Lilith hold's the contract?

Ruby: Yes

Sam: You have two months left Dean. Your not going to hell.

Dean: It's not Ruby it's Lilith.

Lilith: Sick him boys

Dean: I don't know how I got back from hell. All that I know is that I'm back.

Castiel: I'm an angel of the lord Dean. God and the angels got you out of hell for a reason. Were not done with you yet.

NOW: Outside of New York: "They called him the headless horsemen. Legend says that he was a soldier. Who had his head ripped off by a straight cannon ball. Night after night his ghost would ride in the countryside of Sleepy Hollow. Searching for a new head, And a victim to steal it from. Then one lonely Halloween night. Back in the late 1700's, A lonely School master named Ichobod Crane, Was chased down by the demon ghost of the headless horsemen. Ichobod road like crazy to the bridge of souls. A bridge where the horseman could never cross. Because it would send him to hell. But he didn't make it. And poor old Ichobod, Was never seen again. But on every Halloween night. Some people say that the ghost of Ichobod Crane. And the headless horseman. Comes back to ride again in all there glory. Though that's what the legend says. If you believe that sort of thing." Tucker said as he took a sip of what was eight beers that night. He and a few friends thought it would be fun to camp out by the old Graveyard Two nights before Halloween. He was starting to get drunk. "So anybody want to take a stroll over to the bridge of souls? It's not that far from here.

"Ugg please I'd rather take a hot shower. Which will feel good about now." Sarah Michaels said. She was beautiful. Tan body with blonde hair. A senior in high school and on the softball team. Her Boyfriend put his arm around here waist and whispered something in her ear which made her laugh. "You pervert that's what you always think about huh?" She asked.

"Hey I can't help it that my baby is so hot." Mark said. He was very protective of Sarah. Which came to a real problem with Tucker. Since he had a crush on her since the seventh grade. "Hey why don't I walk you home? It's getting late." Mark told her. Sarah nodded and got up. "You coming Tuck?"

"Nahh I think I'm just going to stay out here for awhile and be by myself. Me and my single self." Tucker said. He and his girlfriend Rebecca Jones just broke up about a couple of months ago. It came as a real shock to Tucker since things were going so well. In fact he was thinking about marrying her. And wait until they were done with College. But he was going to ask her after prom. But she suddenly thought that this relationship was going too fast and that was a shock to him.

"Don't stay out too long bro." Mark said as he gave him a high five. Sarah gave him a sympathy wave. Don't get him wrong. He liked Mark. But Sarah was amazing to him. She had always been there for him and she was there for him during the breakup. Tucker had enough and decided to call it a day. I mean it was Halloween tomorrow. His favorite of the year. He was just getting his beer in the back of the truck. He can't let his parents know he was drinking tonight. They would kill him. Then all of a sudden a sound came from behind him. Which sounded like Horse steps?

"No way." Tucker said as he closed the back of his truck. "Mark is that you? Come on guys this is not funny." Tucker said. He walked over to his car door and got a gun out. It had two bullets in it which his father gave him for protection. Since he wasn't the most athletic guy in school. He was even lucky enough to hang with Sarah and Mark. "Hello?" He asked again. He knew he shouldn't be doing this. Something was telling him to go back. That this was against everything in Horror movies. Then with out any warning. A sound of a horse was heard from behind him. As soon as Tucker turned around it was too late. A sword came down on his neck and swiped his head clean off.

"Come on honey I forgot to get my jacket it won't take long." Said Sarah. She really hated it when Mark complained. He was sweet and everything. But damn was he a jerk sometimes. And even too Tucker. As they rounded the corner Sarah immediately saw Tucker's Dead body and began to scream.

SUPERNATURAL

Boston's 'More then a feeling' was playing down a countryside highway as a black Chevy Impala loudly road down the interstate. Sam was Deep in sleep after having a rough night with a demon. But thanks to Ruby's help he was able to vanquish it using his powers with out Dean knowing. Dean looked over at his brother and smiled. This was so easy. He plugged in his brother's headphones to his tape player and put them in his ears. As soon as he was ready he turned the volume up way loud and Sam sat straight up. "God what the hell?"

"Ha Ha, You always make it so easy Sammy." Dean said laughing, "God I love messing with you man."

"You seem awfully cheerful this morning." Sam said taking off his headphones. He had to make sure that he wasn't deaf soon. One day Dean would be the end of him.

"Why do you seem surprised?" Dean asked him like he didn't know what he was talking about.

"Your usually grumpy and don't want to talk. Now your all Mr. Cheerful. Are you sure that Witch we took care of in Salem didn't put you under a spell?"

"Nahh." Dean said leaning his head back against the seat. "It's just that. I don't know. Can't I feel happy for once? I mean with all the Angel stuff and Lilith after us. Don't we deserve to be happy some?"

"Yeah I guess. You sure you don't want to talk about Anna?" Sam asked him. It had been two weeks since Anna went to heaven. Dean didn't talk that much about her or what they did. But let's just say that his impala would never be the same again. He smiled a bit and looked over at Sam.

"No I'm fine. I know she's in a better place and watching over us."

"Um ok." Sam said. This wasn't like Dean at all. Which started to Worry him. "So how far out are we from what's it called again?"

"Sleepy Hollow." Dean said as he continued to drive. "Some people say that there's a horseman that's been roaming around since the 1700's chopping off people's heads. It comes back every Halloween and now there was a person murdered there last night." Dean said.

"Well at least Salem wasn't far from New York." Sam told him as they made pretty good time. "Dean you do know that Sleepy hollow is a legend right? I mean Irvin Washington wrote it as a novel. Do you think that it's really real?" Sam asked

"It wouldn't surprise me. After the shit we have been through in our life." Dean said and poured on the gas.

Author's Note: I would like to thank you guys for reading my first chapter. I've worked hard on this. Please review if you guys can because i love feedbacks. As you can tell i tried to make it more like the show. I even did the recaps and everything. More supernatural characters will appear as the story progresses. Such as Castiel, Anna, Ruby and Bobby. The opening monologue is a homage to the show Are you afraid of the dark. The episode The midnight ride, Had the monologue which Tucker explained the origins of the headless horseman. Anyways please tell me what you think of it. I'll update next week with a new chapter.


	2. Chapter 2

Sam and Dean rolled into town around four. It was just getting dark as it was close to Halloween. Sam and Dean decided to check out the spot where the first body was found but was surprised to see police around the area. Dean looked at Sam and smiled. "FBI or Us marshals?" Sam looked over at his older brother and handed him the FBI badge. They got out of the car and started to walk over to the other officers. The other officers were just as surprised to see them. Sam couldn't help but see from the distance a sobbing Sarah and what appeared to be her boyfriend comforting her.

" Can I help you gentlemen?" The Sherriff spoke as the boys walked up to them.

"Yeah I'm Agent White and this is Agent Black. Were from the FBI. We were wondering if we can look at the body." Dean asked. The Sherriff looked at them with a question glare.

"You boys got here pretty fast didn't you? We just discovered this out last night."

"Yeah well. We work fast." Sam said as the Sherriff walked them over to the body.

"I hope that you have a strong stomach." The sherriff opened the body bag and a roach came out of the head wound. Sam began to choke as Dean looked over at him.

"You ok Agent Black? Not a little stomach sickness are you?"

"Bite me." Sam said as Dean just laughed. He looked over the body and put a napkin over his mouth as well.

"What happened?" He asked the sherriff.

" Far as we could tell he had his head cut off." The sherriff started to explain. Dean was like. 'no duh' "But nobody actually saw anybody do it. I don't know where his Fucking head is." The sherriff said bending down to look at the body. "What kind of a sick person would do that? Killing a human is one thing but taking his or her head. That's another." Dean didn't answer. He looked over to Sarah who was still crying.

"Who is she?" Dean asked. The Sherriff looked over at Sarah.

"She was his friend. The big guy over there with his arm around her is her boyfriend Mark. They were out drinking beer with Tucker and they left for a few moments to head back into town. When they came back. He was dead." Dean became more convinced that it was the horseman by the moment. He took off his medical gloves and walked over to Sam who was standing over by the tree.

"Looks Deffintily like the horseman." Dean said. Sam agreed to this immediately and looked at Dean.

"So you think that the legend is true?" Sam asked him. Dean looked over at Sam and nodded with a smile on his face. "We should talk to some people in town. Maybe they know what is going on." Sam said. Dean agreed to his brother's plan and went over to the Sherriff.

"We will be in touch. You wouldn't happen to know a good motel around here would you?" Dean smiled brightly. The Sherriff showed the boys where the motel was and they drove for fifteen minutes. Sam admired the scenery. It was a nice town and was something different then the city life. He could see himself living out here if he wasn't a hunter. Sam looked over at Dean. He was still worried about his brother. He was different and changed since he came back from hell. Sure the angels had something to do with it. But it was like it wasn't Dean. Sam also was worried about him finding out that he drank demon's blood. More importantly Ruby's. After questioning some of the town folk about Washington Irving and the legend. The boys arrived at the hotel and began to prepare themselves for a long evening worth of sleep. And then start fresh the next morning. Dean had just finished brushing his teeth when the door knocked. Dean already knew who it was as Sam opened the door. "Ruby. Nice to see you again." Dean said to the Burnette demon who walked in the door with her arms folded.

"Hello Dean. I thought we were on a friendly basis." Ruby said, Dean gave her an annoying look and she only smiled with a wave. "Hello Sam." She said as she walked over to where he was sitting and put a hand on his.

"Thanks for coming Ruby. Did you find any information?" Sam asked her. Dean rolled his eyes. He should have known that Sammy called her.

"Yeah I found a couple. The horseman exists. Washington didn't make it up. It was based on a true story. The horseman was a soldier like in the book. How ever he wasn't a hessian like the book said. But a revolutionary soldier. Who fell in love with a Brittish general's daughter. Long story short. The revolutionary soldier got captured by the Brittish General after he had found out about there love affair. And he chopped off his head."

"That's got to suck. So our boy is out there right now chopping off people's heads because he's angry at the Brittish? That doesn't make sense." Dean said.

"I know. Or somebody could be controlling him. Which I doubt it." Sam said looking at Ruby who only shrugged. "So did Icobod really exist? Or was that made up?"

"That I couldn't find out. No body knows if he really existed or not." Ruby said

"Well you're a demon. I thought you were suppose to know everything." Dean said and Ruby glared at him with her dark eyes.

"Just because I'm a demon doesn't mean that I know every person that existed." She said. Ruby looked over at Sam and smiled. "Are you ready to go?" She asked.

"Go? What is she talking about?" Dean asked.

"Dude relax. Were just going out for a couple of burgers and fries." Sam said walking with Ruby to the door. "You want to come?" He asked

"No thanks. I'm not that hungry." Dean said. Sam just nodded and walked out of the door.

"Wow Dean Winchester isn't hungry. That's something new." Ruby said as she left. Dean just mocked her and went to sleep.

OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO

It was late at night and John was getting tired. He couldn't believe that his work had to make him work late. Especially on the week of Halloween. It was usually the most trouble time of the year. Everybody knew that. He looked at his watch and sighed. As he made his rounds around the school building he couldn't wait to get off and see his wife and kids. His wife didn't like him having these late night shifts and it was really starting to put a strain on there marriage. He was just finishing his last round when he heard something in the dark hallway. "Hello?" John asked getting out his flashlight. He looked around the hallway and shrugged as he turned the light off. "It was just the wind." He said to himself. Hoping it was just the wind. As he walked outside he heard another sound. This time it sounded like horse feet. He looked confused for a second and turned around just in time to see a sword coming down on him and chopping off his head.

Author's note: There you go. Chapter two. I hope you guys like it and are still reviewing. I would love more reviews. Sorry for the wait. I had finals and everything.


	3. Chapter 3

Disclaimer: Once again I dont own supernatural. They belong to the CW.

Dean and Sam woke up early in the morning to do sirens blasting across the road next to the motel. Dean was the first one to stir and he moaned. "Did you leave the tv on last night?"

Sam stirred next to him and looked outside. "No man its coming from outside. Something must have happened." Sam said. Dean looked over at him and then groaned. They were able to get dressed and then followed the cops to what it looked like the high school of the town.

"Get ready to go to work Sammy." Dean said as he got out of the car. He looked over to where the dead body was. Once again it was missing a head. He walked over to the Sherriff who looked like he had better days. The Sherriff had noticed them come up.

"Not now boys. I have too much shit on my hands right now. " He said looking down at the dead body.

"When do you want to meet to talk about it Sherriff? Because obviously there is something wrong going on in your town."

"You dont think I know that? I dont want a panic on my hands the night before Halloween. Now look. I apriciate you feds coming here trying to help us out. But I want things to continue to be as normal as possible got it?"

"Yes sir. Again were sorry. Do you mind telling me who the victim was?" Sam asked in a understanding voice. The Sherriff looked at both of them and sighed.

"He was a security guard for our school. The principle made him work late last night. Excuse me guys but I got some buisness to take care of." The Sherriff said and walked away from them. Sam and Dean looked at each other and saw that the high school kids were just getting here for the morning school hours.

"So What do you think Dean? Horsemen?"

"Looks like it doesnt it? It fits the pattern." Dean said as he began to walk away from the crime scene.

　"It just doesnt make any sense. I mean the horseman guy was real but there was no Ichobod. I dont get it." Sam said

"Who says Ichobod didnt exist? I mean maybe he escaped the ride of death and moved away from Sleepy hollow." Dean told him.

"What are you saying Dean?" Sam asked

"What Im Saying is that maybe, Ichobod Crane was Washington Irving." Dean said. Sam looked at Dean with a look that maybe he was right.

"Huh, And I thought I was the smart one." Sam said.

"Hey I studied. Come on. I hate to say this but lets go to the library and see if we can find anything." Dean said. As they walked through the hallways of the school they ran into a familiar person. And they all fell onto the floor. Dean was the first one to help her on her feet. "Sarah?" Dean asked.

"You guys? The FBI agents right?" Sarah asked as she picked up her books.

"Yep that would be us. Um Im Dean this is my partner Sam. Incase you dont remember our names. We were on our way to the library to look up some stuff on the case."

"I could join you. I was just going there anyways." Sarah said and then Dean told her to lead the way since she went there. "So. Any luck on our case?" Sarah asked trying to make small talk.

"Not really. Its kind of confusing to say the least. But we do have one theory." Sam said as the three started to walk to the library.

"What is it?" Sarah asked.

"Well we do believe that there really was a Ichobod Crane that lived in Sleepy Hollow. But he never died from the horseman and escaped. He got married and New York and had a couple of grandchildren." Sam began to explain

Dean got annoyed by his brothers rambling and interrupted him. "In short Term Sarah and not the neardy term. We believe that Washington Irving was Ichobod Crane. Irving Changed his name because he wanted to keep his family safe from the horseman."

"Really? That is interesting. But why is the horseman back all of the sudden? I mean it doesnt make since for him to be back. Although it is the Anniversery of there famous ride." She said.

"Really? We didnt know that." Sam said. That was a new theory to say the least.

"Yeah. Anways here is the library." Sarah said as she dropped some books off there and looked at Sam and Dean. "Thanks for Caring about our town. I have to meet my boyfriend at the big Pep rally today. Im still cheering." Sarah said as she smiled showing the brothers her pomp pomps.

"Hey how are you doing? With Tuckers Death and everything." Dean asked her in a caring mode.

"Im doing ok. Just a little upset you know? So is Mark. Its going to take awhile to get over his death. But I just couldnt be at home all day our I would loose my mind you know?"

"Yeah I know the feeling." Sam said looking at Dean. "Take care Sarah. Be careful tonight." Sam told her. Sarah nodded to him and then handed him a orange paper.

"Tonight is our haunted hayride we do every night before Halloween. You can come if you want. Mark is doing the Storytelling." She said with a smile on her face and then walked away.

OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO

Sam and Dean spent hours in the library researching on every legend possible on the headless horsemen. They finally found something that looked like it would be there match. "See I told you we would find something." Dean said as Sam walked over to the librarian and asked for her to print this information out for them.

"So Ichobod did exist huh?" Dean said as Sam came back with the information.

"Yeah and look at this. It says here that Ichobod escaped his fateful ride and Moved to New York City right after the event. Just up and left. Thats why people said he disappeared."

"Thats interesting." Dean said

"The twist gets better. It says that he was worried about The horseman coming after his family. So he changed his name to Washington Irving. And he wrote the Novel a couple of years later so people would think the horseman was a fake and not real." Sam said. Dean looked over at him and smiled.

"Your loving this arent you M. Night?" Dean asked.

"Yeah well. It still doesnt explain why the horseman is back after being dormented in Hell for all these years." Sam said and then got an idea. He looked over at Dean and smiled.

"You have a theory dont you theory boy?" Dean asked him. Sam nodded and He looked over at The librarian and smiled. "Can I see the family records please of the area over the last two hundred years?" Sam asked. The librarian handed him a hell of a lot of records and Dean moaned.

"Were going to have to look through everyone of these are we?" He asked.

"Yep get ready." Sam said, Sam and Dean spent another two hours flipping through the records and then they found what they were looking for.

"Bingo." Sam said in an excited voice. "Right here look at this. It says that after Icobod change the familys last name to Craneston. And then his son changed his name to Irving."

Dean smiled as he sat back in the chair. "As in Washington Irving."

"Bingo." Sam said all happy about himself.

"Alright so what if Washington Irving was the son of Ichobod Crane. Whats next for the horseman?"

"To kill the next living decendent of Ichobod and cut off peoples head in the process. Or who ever gets in his way."

"The Hayride." They said together.

"Damn I hate it when we say words together. Its creepy." Dean said. They began to clean the mess up and Sam looked at his watch.

"Ok its Three right now." The hayride starts around Seven.

"And who is the next living realitive of Ichobod?" Dean asked.

"Well according to the records its." Sam stopped and looked at Dean. "Its Sarah." Sam said and then Dean nodded as they walked out of the library.

"We have to find her and tell her about the legend." Dean said.

"Shes not going to believe us Dean. I mean I know about it and I hardly believe it." Sam said

"Well we have to convince her. You have to Convince her. Shes at that pep rally right now remember? Shes a cheerleader." Dean said getting in the impala. Sam just stared at him.

"What where are you going?" He asked

"Going to the Sherriff's station and try to convince him to shut down the hayride. Go if you convince her bring her to the motel."

"And if I dont convince her?" Sam asked and Dean gave him a look.

"Knock her out anyways." He said and then road off.

Authors note: Another chapter. Sorry for the delay again. Im finally done with school. Some help and pointers would work. And positive feedback as well. Please review.


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